From Brooklyn to Churchill Downs: A lawyer ‘Always Dreaming’ of success

From his thick Brooklyn accent to his maddening 18-hour-a-day schedule, Anthony Bonomo is a New Yorker through and through.

But inner-city dwellers are hardly known for their horse riding prowess: Bonomo’s main exposure to horses as a kid was watching them pull fruit carts.

So how did a malpractice lawyer from Williamsburg, just across the East River from Manhattan, end up owning Always Dreaming, the 6-to-1 favorite in Saturday’s Kentucky Derby?

“In my wildest dreams, did I ever think that I would own a racehorse? No,” Bonomo tells CNN, as he jumps in a yellow cab in between meetings in Manhattan. “Did I ever think that I’d own racehorses that would be as competitive as we have been? No.”

Bonomo’s naivete is reflected in the name of his stable: Brooklyn Boyz, which evokes memories of rap groups from the 1980s and 1990s rather than the rarefied air of the Kentucky elite. (For the record, he is more a fan of the Eagles than Brooklyn’s Beastie Boys.)

The 59-year-old attributes most of his racing success to his wife Mary Ellen who introduced him to the sport in 2005. The couple took a trip upstate to Saratoga Springs, the horse racing capital of the East Coast, where they “fell in love” with the town.

“The reason I’m involved is because of her,” Bonomo says. “She said, ‘I’d love to own a horse.’ You know, when you love somebody you do what they ask. So, we went into horse racing and we’ve been very fortunate.”

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A family affair

The relationship between the spouses was competitive from the start, with each forming their own stable. “Early on she liked certain horses and I didn’t,” explains Bonomo.

Their son, Anthony Bonomo Jr., had just graduated from college and got into the business, too, as an assistant trainer – for his mother.

“He favors his mom a little bit; he’s not stupid,” says Bonomo, explaining how the family divide was short-lived. “I noticed she was winning a lot more than me, so I thought ‘When all else fails, join.’”

The couple currently split ownership of all their horses, occasionally allowing external investors to join them. (Always Dreaming is partially owned by longtime friend Vinnie Viola, along with two other minority stakeholders.)

“Partners in life, partners in this,” Bonomo says, noting that racing’s greatest gift to him has been the family bonding experience. Along with Anthony Jr., who now attends law school in New York, the couple have two daughters, one a lawyer, the other a small animal vet.

“The horse racing business for me has been more about bringing our family together to rally around something,” he says, “so it’s been kind of cool.”

Always Dreaming, who won both his races this year including the Florida Derby, is sired by 2012 Kentucky Derby runner-up Bodemeister and was purchased at the Keeneland auction on the recommendation of bloodstock agents, as well as Anthony Jr.

“He just stood out,” says Bonomo, who stresses there was a lot of “guesswork” involved. “There are certain attributes that you say are good, but you don’t know what that horse is going to do.

“As he progressed and started to grow and run, he just got better and better with every race.”

What’s in a name?

As for his starry-eyed moniker, Bonomo again gives credit to Mary Ellen.

“My wife picks out most of the names,” he explains. “I wasn’t about to say anything. When she comes up with the idea, that’s it.

“It was always our dream to get a horse in a big race, and we’re always dreaming in life, not just in horse racing. Every day, aren’t you dreaming about something?”

Mary Ellen – whose dream will come true this weekend at The Run for the Roses – had previously picked the names for Escape from Reality and last year’s big hope Greenpointcrusader.

Named after a Brooklyn enclave near Williamsburg, Greenpointcrusader was set to enter the 2016 Kentucky Derby as a favorite until suffering an injury at the Louisiana Derby just five weeks earlier.

“I never thought I’d have a horse like that, and to come back this year with a horse like (Always Dreaming), it’s amazing,” says Bonomo, who has spared no expense this year.

‘Unsung heroes’

Although Always Dreaming is being looked after by esteemed trainer Todd Pletcher and ridden by Hall of Fame jockey John Velazquez, Bonomo emphasizes that it’s all the handlers behind the scenes who make the difference.

“What we don’t do in this business is recognize the hard work every day, not only of the trainers and the jockeys, but all people who work in the barns, the grooms, the hot walkers – they are the unsung heroes of racing,” he says.

“They do a lot for these horses that keeps them unnoticed by a lot of people.”

Considering his working-class roots, it’s not surprising that Bonomo prefers to deflect attention. When asked whether any clients of his law practice are aware that he is a big player in horse racing – his stable owns around 25 thoroughbreds – he laughs off the suggestion.

“I’m not a big-time horse guy, I’m a horse guy who got lucky,” he says. “You’re at the top one day, and down at the bottom another day, so you’ve got to take it when you get it.”

Although Bonomo is not about to give up his day job anytime soon, he says that Brooklyn Boyz Stables is very much a self-sustaining business.

“My ultimate goal is to buy one or two horses like (Always Dreaming) every year, but that’s not realistic,” he says.

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“No pun intended, but we’re always dreaming about this horse’s ability and where he is going to go.”